The total synthesis of (-)-tetrahydrolipstatin

Jennifer A. Bodkin; Edward J. Humphries; Malcolm D. McLeod

doi:10.1016/S0040-4039(03)00443-X

The total synthesis of (-)-tetrahydrolipstatin

Jennifer A. Bodkin, Edward J. Humphries, Malcolm D. McLeod^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

Careful control during the bromolactonisation of β,γ-unsaturated acid 3 was required to afford regioselectively the trans-β-lactone 4 as the major diastereomer. Radical debromination of 4 followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin.

Original language	English
Pages (from-to)	2869-2872
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(03)00443-X
Publication status	Published - 31 Mar 2003
Externally published	Yes

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10.1016/S0040-4039(03)00443-X

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title = "The total synthesis of (-)-tetrahydrolipstatin",

abstract = "Careful control during the bromolactonisation of β,γ-unsaturated acid 3 was required to afford regioselectively the trans-β-lactone 4 as the major diastereomer. Radical debromination of 4 followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin.",

keywords = "(-)-tetrahydrolipstatin, Bromolactonisation, Radical dehalogenation, β-lactone",

author = "Bodkin, {Jennifer A.} and Humphries, {Edward J.} and McLeod, {Malcolm D.}",

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AU - Bodkin, Jennifer A.

AU - Humphries, Edward J.

AU - McLeod, Malcolm D.

PY - 2003/3/31

Y1 - 2003/3/31

N2 - Careful control during the bromolactonisation of β,γ-unsaturated acid 3 was required to afford regioselectively the trans-β-lactone 4 as the major diastereomer. Radical debromination of 4 followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin.

AB - Careful control during the bromolactonisation of β,γ-unsaturated acid 3 was required to afford regioselectively the trans-β-lactone 4 as the major diastereomer. Radical debromination of 4 followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin.

KW - (-)-tetrahydrolipstatin

KW - Bromolactonisation

KW - Radical dehalogenation

KW - β-lactone

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U2 - 10.1016/S0040-4039(03)00443-X

DO - 10.1016/S0040-4039(03)00443-X

M3 - Article

SN - 0040-4039

VL - 44

SP - 2869

EP - 2872

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

The total synthesis of (-)-tetrahydrolipstatin

Abstract

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